"No Prison is big enough to hold the Boss." In on one side, and out at the other.

This Harper’s Weekly cartoon by Thomas Nast predicts that the legal authorities of New York City will not be able to keep William Tweed, the corrupt boss of Tammany Hall, in jail.

In the 1860s and early 1870s, William Tweed ran Tammany Hall, the powerful Democratic political machine in New York City, and served as the city’s public works commissioner and as a state senator (1867-1871). The name of Boss Tweed and his bulky visual caricature became synonymous with political corruption and greed, an association that remains potent even today. This is thanks in large part to the creatively memorable cartoons drawn by Thomas Nast for Harper’s Weekly.

As political boss, Tweed used his formal and informal authority to gain financial profit for himself and his Tammany Hall cohorts. The Tweed Ring, as they became known, extorted a reported $6 million from the public treasury, although more recent estimates put the figure between $30 to $200 million. Tweed became one of New York City’s largest landowners by the late 1860s, and spent his ill-gotten gain lavishly, living in a mansion on Fifth Avenue and wearing a large diamond stud on his shirt.

Although criticized by good-government reformers, the Tweed Ring found support among the working class, many of whom were immigrants, by providing jobs and basic necessities like food and fuel, establishing the Manhattan Eye and Ear Hospital, and expanding the number of public baths, almshouses, and orphanages in the city. However, in the less than three years of the height of the Tweed Ring’s power (1869-1871), New York City’s debt tripled and its taxes rose accordingly.

The downfall of the Tweed Ring came when disgruntled Tammany Hall members leaked incriminating evidence to the New York Times, which published a series of damning articles beginning in July 1871. Harper’s Weekly and other newspapers joined the Times to expose the scandal, and Tweed allegedly most feared “those damned pictures” by Harper’s Weekly cartoonist Thomas Nast.
In November 1871, Tweed was reelected to another term in the state senate. In general, though, the press campaign against the Tweed Ring was successful, with most Tammany Hall candidates losing in the fall election. In December, Tweed was arrested on fraud charges, and forced to resign as public works commissioner, state senator, and head of Tammany Hall.
The first criminal trial against Tweed resulted in a hung jury, but the second ended with a conviction on misdemeanor charges. The sentence was a $12,500 fine and 13 years in jail, which in 1875 an appeals court deduced to $250 and one year. Since he had already served 19 months in the city jail on Blackwell’s Island, he was released. The police, however, rearrested him the next day to stand trial on the civil charges.

Being unable to raise the $3 million bail, Tweed ended up in Ludlow Street jail. He was granted privileges and liberties not allowed to other inmates, such as carriage rides and visits to his home and those of his adult children. On December 4, 1875, he escaped while on such a sojourn and hid out in New Jersey.

In March 1876, the civil jury found Tweed guilty and liable for over $6 million. Learning of the judgment, he fled to Cuba, then Spain. In September, Spanish officials arrested and deported him, mistakenly identifying him (through a Nast cartoon) as a child abductor. Back in New York by late November, he was placed in the Ludlow Street jail again.

In poor health, Tweed gave the attorney general, Charles Fairchild, a full confession as part of a deal for his release. Fairchild, however, changed his mind and Tweed remained in prison. The former political boss later testified before a Board of Aldermen investigation, detailing how the ring operated, but he received no pardon for his cooperation. In April 1878, he died in Ludlow Street jail of heart failure caused by pneumonia.